Cyclopropyl In Acid Moiety Patents (Class 560/124)
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Patent number: 5653990Abstract: There is provided an ester compound represented by the formula I: ##STR1## wherein R.sub.1 is a methyl group or a hydrogen atom; R.sub.2 is a C.sub.1-6 haloalkyl group; and R.sub.3 is a pyrethroid acid residue, an agent for controlling noxious organisms containing the same as active ingredient and an intermediate for producing the same.Type: GrantFiled: June 21, 1995Date of Patent: August 5, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Kazunori Tsushima, Takashi Furukawa, Takao Ishiwatari, Toru Tsuchiya, Mikako Nakamachi
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Patent number: 5648387Abstract: Dialkyl ethers lower Lp(a) and triglycerides, and elevate HDL-cholesterol, and are thereby useful for treating vascular diseases and noninsulin-dependent diabetes mellitus.Type: GrantFiled: March 24, 1995Date of Patent: July 15, 1997Assignee: Warner-Lambert CompanyInventors: Charles Larry Bisgaier, Paul Leroy Creger, Alan Robert Saltiel, Sherrie Rae Tafuri
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Patent number: 5626834Abstract: A snake-controlling agent contains at least one pyrethroid compound as an active ingredient. It is used for controlling snakes. According to the present invention, the effective controlling of snakes is possible by utilizing the snake-controlling property of pyrethroid compounds.Type: GrantFiled: July 30, 1992Date of Patent: May 6, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Michihisa Toriba, Kenji Tsuda, Satoshi Senbo, Yoshiaki Kosuge, Hiroshi Fukui, Yoichiro Tsubaki
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Patent number: 5623087Abstract: A method for preparing a diarylalanine compound is provided. The method includes reacting a diarylaminopropanediol with a reducing agent to form a diarylaminopropanol compound and/or contacting a serine ester derivative with an aryl metal reagent to form diarylaminopropanediol. A diarylmethyloxazolidinone compound is also provided.Type: GrantFiled: March 10, 1995Date of Patent: April 22, 1997Assignee: NDSU-Research FoundationInventors: Mukund P. Sibi, Prasad K. Despande, Anthony J. LaLoggia
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Patent number: 5616607Abstract: Compounds of the general structure ##STR1## are disclosed, wherein X is O, C.sub.n, NH, or S, wherein n is 1, 2, 3 or 4; R1 is OH, CH.sub.3, CH.sub.2 OH, N.sub.3 or CH.sub.2 N.sub.3 ; R3 is H or CH.sub.3 ; R5 is Y-R2, wherein Y is a six-carbon chain optionally containing up to three double or triple bonds or a mixture of double and triple bonds up to a maximum of three; R2 is C.sub.1 -C.sub.10 alkyl OH, C.sub.1 -C.sub.10 alkyl N.sub.3 or COOR4, wherein R4 is H, a branched or unbranched C.sub.1 -C.sub.10 alkyl (including substituted alkyl radicals), cycloalkyl, preferably C.sub.5 or C.sub.6 cycloalkyl, or a five- or six-membered aryl radical (including substituted aryl radicals), i.e. R2 is COOH or an ester of R4; R6 is a seven-carbon chain optionally containing up to three double or triple bonds or a mixture of double and triple bonds up to a maximum of three; and . . . . . . indicates a single, double or triple bond.Type: GrantFiled: March 21, 1995Date of Patent: April 1, 1997Assignee: HSC Research and Development Limited PartnershipInventors: Cecil R. Pace-Asciak, Peter M. Demin
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Patent number: 5610188Abstract: Compounds of the formula ##STR1## wherein the variables are defined in the specification. The compounds and their salts are soft anticholinergic/antisecretory agents especially useful as mydriatics and as antiperspirants.Type: GrantFiled: December 30, 1994Date of Patent: March 11, 1997Assignee: University of FloridaInventors: Richard H. Hammer, Nicholas S. Bodor
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Patent number: 5578595Abstract: Novel 2-(2,2-difluorocyclopropyl)-acetic acid derivatives of formula I ##STR1## wherein A is oxygen or --NR.sub.1 --,B is C.sub.2 -C.sub.6 alkylene,D is oxygen, sulfur or --O--CH.sub.2 --,E is phenyl; phenyl substituted by from one to three substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 haloalkyl and C.sub.1 -C.sub.4 alkoxy; a five-membered aromatic heterocycle having from one to three hetero atoms selected from the group nitrogen, oxygen and sulfur; a five-membered aromatic heterocycle having from one to three hetero atoms selected from the group nitrogen, oxygen and sulfur that is substituted by one or two substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.3 haloalkyl; a six-membered aromatic heterocycle having from one to three nitrogen atoms; or a six-membered aromatic heterocycle having from one to three nitrogen atoms that is substituted by one or two substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl and C.Type: GrantFiled: March 21, 1995Date of Patent: November 26, 1996Assignee: Ciba-Geigy CorporationInventor: Manfred B oger
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Patent number: 5565490Abstract: p-Hydroxyaniline derivatives of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is hydrogen, or unsubstituted or substituted alkyl;R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl,OR.sup.5 or NR.sup.6 R.sup.7, whereR.sup.5, R.sup.6 are unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, andR.sup.7 is hydrogen or alkyl,and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests, and also compounds of the formula VI ##STR2## and their salts, processes for their preparation, compositions containing them and their use as intermediates and for controlling pests are described.Type: GrantFiled: November 10, 1994Date of Patent: October 15, 1996Assignee: BASF AktiengesellschaftInventors: Oliver Wagner, Karl Eicken, Norbert G otz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5550258Abstract: The present invention provides an ester compound represented by a formula I: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group, or a C.sub.1 -C.sub.1 6 alkyl group which may be substituted with at least one halogen atom; and R.sub.3 represents an acid residue of pyrethroids.The invention also relates to an active agent for controlling noxious insect pests containing the ester compound as an active ingredient, an intermediate for production of the ester compound and a process for producing the intermediate. The ester compound represented by the formula I has good activities for controlling noxious insect pests.Type: GrantFiled: August 23, 1994Date of Patent: August 27, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
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Patent number: 5534188Abstract: An acetylene derivative represented by general formula (I): ##STR1## wherein R.sup.1 is saturated or unsaturated alkyl group having 3-20 carbon atoms, R.sup.2 is saturated or unsaturated alkyl group having 1-20 carbon atoms which may optionally be substituted by halogen atom or alkoxyalkyl group having 2-20 carbon atoms, A and B represent phenylene group or the like or taken as --A--B-- represent naphthalene group or the like, m and s are each 0 or 1, n is integer of 1-6, and * means asymmetric carbon atom; a process for producing said acetylene derivative, a liquid crystal composition using the same as active ingredient, and a liquid crystal element using said composition.Type: GrantFiled: June 24, 1994Date of Patent: July 9, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Takayuki Higashii, Shoji Toda, Naoyuki Takano, Kayoko Ueda, Koichi Fujisawa
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Patent number: 5530022Abstract: A compound in all possible stereoisomeric forms and their mixtures of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## having excellent pesticidal, particularly insecticidal, properties.Type: GrantFiled: August 9, 1994Date of Patent: June 25, 1996Assignee: Roussel-UclafInventors: Didier Babin, Marc Benoit, Jean P. Demoute
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Patent number: 5510509Abstract: Dialkyl cyclopropane-1,1-dicarboxylates are prepared from a dialkyl malonate, a 1,2-dichloroalkane and finely divided potassium carbonate while azeotropically removing the water released by the reaction.Type: GrantFiled: August 8, 1994Date of Patent: April 23, 1996Assignee: Huls AktiengesellschaftInventor: Klaus-Dieter Steffen
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Patent number: 5504112Abstract: A compound in all possible stereoisomeric forms and their mixtures of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, --CN, alkyl, alkenyl and alkynyl of up to 4 carbon atoms and aralkynyl of up to 10 carbon atoms, Y is selected from the group consisting of halogen, --CF.sub.3, --CH.sub.2 F and --CHF.sub.2 and R.sub.1 is hydrogen and R.sub.2 is halogen or R.sub.1 and R.sub.2 are --CF.sub.3 or R.sub.1 and R.sub.2 are individually halogen.Type: GrantFiled: May 15, 1995Date of Patent: April 2, 1996Assignee: Roussel UclafInventors: Didier Babin, Marc Benoit, Raphael Bouchet, Jean-Pierre Demoute
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Patent number: 5498750Abstract: A new process for the preparation of 1-fluoro-cyclopropane-1-carboxylic acid of the formula ##STR1## which process comprises a) reacting in a first step, a 1-fluoro-cyclopropyl phenyl ketone of the formula ##STR2## in which R represents hydrogen, halogen, methyl, methoxy, phenyl or phenoxy, with an peroxy compound in the presence of a diluent, andb) reacting, in a second step, the resulting 1-fluoro-cyclopropane-1-carboxylate of the formula ##STR3## in which R has the abovementioned meaning, with a base in the presence of a diluent, and then acidifying the mixture. New 1-fluoro-cyclopropane-1-carboxylates of the above-mentioned formula.Type: GrantFiled: March 15, 1995Date of Patent: March 12, 1996Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5468905Abstract: Compounds represented by general formulas (I) and (II), useful as the intermediates for agricultural chemicals, particularly herbicidal compounds, wherein R.sup.1 and R.sup.2 represent each hydrogen, alkyl or COOR.sup.3 :R.sup.3 represents alkyl: and R.sup.4 represents alkyl.Type: GrantFiled: May 25, 1994Date of Patent: November 21, 1995Assignee: Nippon Soda Co., Ltd.Inventors: Junji Suzuki, Masami Hatano, Shinichi Imaizumi
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Patent number: 5453464Abstract: This invention provides the use and preparation of certain 2,2'-diacetyl-bisacetoacetates and bis(beta-ketoesters). These compounds are useful in coating formulations as crosslinkers in conjunction with polyester, acrylic and/or other hydroxylated resins to provide coatings that cure at about 100.degree. and 175.degree. C. Certain combinations of these crosslinkers and resins cure at unusually low temperatures and provide films with good combinations of flexibility, hardness and adhesion.Type: GrantFiled: April 28, 1994Date of Patent: September 26, 1995Assignee: Eastman Chemical CompanyInventors: J. Stewart Witzeman, Allen L. Crain
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Patent number: 5434267Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.Type: GrantFiled: March 14, 1994Date of Patent: July 18, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
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Patent number: 5434303Abstract: A new process for the preparation of 1-fluoro-cyclopropane-1-carboxylic acid of the formula ##STR1## which process comprises a) reacting in a first step, a 1-fluoro-cyclopropyl phenyl ketone of the formula ##STR2## in which R represents hydrogen, halogen, methyl, methoxy, phenyl or phenoxy,with an peroxy compound in the presence of a diluent, andb) reacting, in a second step, the resulting 1-fluoro-cyclopropane-1-carboxylate of the formula ##STR3## in which R has the abovementioned meaning,with a base in the presence of a diluent, and then acidifying the mixture.New 1-fluoro-cyclopropane-1-carboxylates of the above-mentioned formula.Type: GrantFiled: November 24, 1993Date of Patent: July 18, 1995Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5420159Abstract: All possible stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl of up to 4 carbon atoms, --CN and aralkynyl of up to 10 carbon atoms, Y is selected from the group consisting of halogen, --CH.sub.2 F, --CHF.sub.2, and --CF.sub.3, A is selected from the group consisting of ##STR2## having pesticidal properties.Type: GrantFiled: September 26, 1994Date of Patent: May 30, 1995Assignee: Roussel-UclafInventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute
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Patent number: 5412120Abstract: A process for preparing monocarboxylic esters of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.8 -cyclo-alkyl acyl, aryl or C.sub.7 -C.sub.20 -aralkyl or together --(CH.sub.2).sub.n --X--(CH.sub.2).sub.m --,X is methylene, oxygen, sulfur, NH or NR.sup.3,R.sup.3 is C.sub.1 -C.sub.12 -alkyl, andn and m are each from 0 to 8, comprises reacting geminal dicarboxylic esters of the general formula II ##STR2## where R.sup.1 to R.sup.3 are each as defined above, at from 150.degree. to 400.degree. C. in the presence of catalysts.Type: GrantFiled: November 29, 1993Date of Patent: May 2, 1995Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Norbert Goetz, Thomas Kuekenhoehner, Werner Schnurr
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Patent number: 5395958Abstract: The cyclopropene derivatives of the present invention are useful as the intermediates for producing cyclopropenone derivatives exhibiting strong inhibition activity of thiol protease such as calpain, papain, cathepsin B, cathepsin H, cathepsin L and the like.Type: GrantFiled: September 27, 1993Date of Patent: March 7, 1995Assignee: Mitsubishi Kasei CorporationInventors: Ryoichi Ando, Yasuhiro Morinaka, Eiichi Nakamura
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Patent number: 5391571Abstract: The compounds of the formula: ##STR1## in which R.sup.1 is alkyl of 4 or more carbon atoms, cycloalkyl, 1-adamantyl, 2-adamantyl, 3-noradamantyl, 3-methyl-1-adamantyl, 1-fluorenyl, 9-fluorenyl, cycloalkylalkyl, phenyl, substituted phenyl, alkyl, alkoxy, halo, nitro, cyano or trifluoromethyl, phenylalkyl or substituted phenylalkyl, where the substituent on the benzene ring is alkyl, alkoxy, halo, nitro, cyano, trifluoromethyl or phenyl; R.sup.2 is hydrogen, alkyl or R.sup.1 taken with R.sup.2 and the nitrogen atom to which they are attached form a heterocyclic moiety of the formula: ##STR2## wherein ##STR3## in which R.sup.7 is hydrogen, alkyl, hydroxy, alkanoyloxy, hydroxyalkyl, hydroxycarbonyl, alkoxycarbonyl, phenyl or substituted phenyl, in which the substituent is alkyl, alkoxy, halo, nitro, cyano, haloalkyl, perhaloalkyl or dialkylaminoalkyl; R.sup.8 is hydrogen or alkyl or R.sup.7 and R.sup.8 taken together are polymethylene; R.sup.Type: GrantFiled: May 13, 1993Date of Patent: February 21, 1995Assignee: American Home Products CorporationInventors: Richard E. Mewshaw, Thomas J. Commons, Donald P. Strike
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Patent number: 5371270Abstract: A method of manufacturing chlorine-free cyclopropanecarboxylic acid methyl ester is described wherein a first portion of alkali methoxide is added to a high-boiling solvent, followed by a second portion of methoxide with an equimolar portion of 4-chlorobutyric acid. The ester product can be readily hydrogenated catalytically to the corresponding carbinol.Type: GrantFiled: May 11, 1993Date of Patent: December 6, 1994Assignee: Huels AktiengesellschaftInventors: Manfred Kaufhold, Josef Metz
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Patent number: 5352822Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.Type: GrantFiled: April 7, 1993Date of Patent: October 4, 1994Assignee: Roussel UclafInventors: Robert J. Blade, George S. Cockerill, John E. Robinson
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Patent number: 5336670Abstract: Compounds of the formula ##STR1## wherein X is hydrogen, halogen or an optionally substituted alkyl, Y is selected from the group consisting of hydrogen, halogen optionally substituted alkyl, an optionally substituted aryl or arylalkyl, --(CH.sub.2).sub.m Si (Alk.sub.1).sub.3, --(CH.sub.2).sub.n OAlk.sub.2 or --(CH.sub.2).sub.p SAlk.sub.3, m, n and p are an integer from 0 to 6, Alk.sub.1, Alk.sub.2 and Alk.sub.3 are alkyl and R is alkyl of 1 to 18 carbon atoms or the remainder of an alcohol used in the pyrethrinoid series having pesticide properties.Type: GrantFiled: December 17, 1992Date of Patent: August 9, 1994Assignee: Roussel-UclafInventors: Marc Benoit, Jean-Pierre Demoute, Jean-Marc Girodeau
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Patent number: 5326901Abstract: Novel 2-(2,2-difluorocyclopropyl)-acetic acid derivatives of formula I ##STR1## wherein A is oxygen or --NR.sub.1 --,B is C.sub.2 -C.sub.6 alkylene,D is oxygen, sulfur or --O--CH.sub.2 --,E is phenyl; phenyl substituted by from one to three substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 haloalkyl and C.sub.1 -C.sub.4 alkoxy; a five-membered aromatic heterocycle having from one to three hetero atoms selected from the group nitrogen, oxygen and sulfur, a five-membered aromatic heterocycle having from one to three hetero atoms selected from the group nitrogen, oxygen and sulfur that is substituted by one or two substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.3 -haloalkyl; a six-membered aromatic heterocycle having from one to three nitrogen atoms; or a six-membered aromatic heterocycle having from one to three nitrogen atoms that is substituted by one or two substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl and C.Type: GrantFiled: March 22, 1993Date of Patent: July 5, 1994Assignee: Ciba-Geigy CorporationInventor: Manfred Boger
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Patent number: 5312964Abstract: A novel process for the preparation of isomers or mixtures of isomers of compounds of the formula ##STR1## and novel intermediates therefore.Type: GrantFiled: May 27, 1993Date of Patent: May 17, 1994Assignee: Roussel UCLAFInventors: Didier Babin, Neerja Bhatnagar, Francis Brion, Colette Colladant
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Patent number: 5292928Abstract: In a process for reacting a low molecular weight hydroxy compound with a carboxylic acid halide, a small amount of the acid halide is introduced into the reaction vessel and the remainder of the acid halide and the hydroxy compound are added gradually in an approximately stoichiometric ratio. The hydrogen halide formed is thus prevented from dissolving in the reaction medium. The heat of reaction to be dissipated is negligible.Type: GrantFiled: July 31, 1992Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventor: Karlheinz Miltenberger
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Patent number: 5286746Abstract: Antihypercholesterolemic activity is exhibited by compounds of the formula ##STR1## wherein: X is hydrogen, alkali metal or ammonium;Y is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl; ##STR2## R is hydrogen, alkyl, ammonium, alkylammonium, or alkali metal (such as Na, Li, or K); andn is 1 or 2.Type: GrantFiled: December 20, 1991Date of Patent: February 15, 1994Assignee: E. R. Squibb & Sons, Inc.Inventor: Kathleen M. Poss
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
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Patent number: 5264152Abstract: An optically active compound represented by the formula (I): ##STR1## wherein R is a straight or branched chain alkyl or alkoxy group having 1 to 15 carbon atoms, ##STR2## is a 1,4-cyclohexylene or 1,4-phenylene group, ##STR3## is a 1,4-phenylene or 3-fluoro-1,4-phenylene group, X is a mono-, di- or tri-fluoromethyl group, W is a straight or branched chain or cyclic alkylene group having 1 to 16 carbon atoms or a straight or branched chain alkenylene group having 2 to 16 carbon atoms, Y is a bond or --COO--, and Z is a straight or branched chain alkyl group having 1 to 8 carbon atoms, a phenyl group or a hydrogen atom, which is useful as a component of ferroelectric liquid crystal compositions or as a device utilizing said composition.Type: GrantFiled: April 7, 1992Date of Patent: November 23, 1993Assignee: Sharp Kabushiki KaishaInventors: Makoto Shiomi, Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
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Patent number: 5262438Abstract: All possible stereoisomers and mixtures thereof of a compound of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, fluorine, chlorine and bromine, R is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl and cycloalkyl of up to 8 carbon atoms, optionally substituted aryl and aralkyl of up to 14 carbon atoms and optionally substituted heterocyclic and Z is selected from the group consisting of hydrogen, methyl, --CN and --C.tbd.CH having pesticidal, particularly insecticidal properties.Type: GrantFiled: July 1, 1992Date of Patent: November 16, 1993Assignee: Roussel-UCLAFInventors: Marc Benoit, Jacques Demassey, Jean-Pierre Demoute
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Patent number: 5247125Abstract: Novel thiol-terminated hydroxyamides, and processes for their preparation and use are provided. These hydroxyamide compounds may be prepared by the reaction of a mercapto-functional alkyl ester, such as methylmercaptopropionate, with a molar excess of an alcohol-substituted amine, such as a b-hydroxyalkyl amine. The thiol-terminated hydroxyamides are useful as polymerization chain transfer agents, particularly when it is desirable to form polymers or oligomers containing functional hydroxyamide end groups. By chain terminating such polymers or oligomers with reactive hydroxyamide end groups the polymers or oligomers can be further reacted with acid-containing monomers or polymers to form block or graft copolymers.Type: GrantFiled: February 28, 1991Date of Patent: September 21, 1993Assignee: Rohm and Haas CompanyInventors: Andrew W. Gross, William D. Emmons
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Patent number: 5245073Abstract: Novel 2,2-dimethyl-cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually halogen, R.sub.1 is selected from the group consisting of halogen, alkyl of 1 to 8 carbon atoms, optionally substituted aryl of 6 to 14 carbon atoms, perfluoroalkyl of 1 to 8 carbon atoms, --CN and ##STR2## R' is alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of --SO.sub.2 Alk.sub.1, --SO.sub.2 Ar, ##STR3## Alk.sub.1 is optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted with at least one halogen, Ar is aryl of 6 to 14 carbon atoms optionally substituted with at least one halogen Alk.sub.2 and Alk.sub.3 and Alk.sub.2 ' and Alk.sub.Type: GrantFiled: August 20, 1991Date of Patent: September 14, 1993Assignee: Roussel UclafInventors: Joseph Cadiergue, Jean-Pierre Demoute, Jean Tessier
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Patent number: 5238957Abstract: New esters of 2,2-dimethyl-cyclopropane-carboxylic acid, which are endowed ith insecticidal and acaricidal activity, have the general formula: ##STR1## wherein: represents ##STR2## or aR.sub.1 --Y--CF.sub.2 --C.tbd.C--group;Y represents either O or S;X represents H, F, Cl, Br, or --CF.sub.3 ;R.sub.1 represents either a linear or a branched (C.sub.1 -C.sub.6)-aklyl group, or a (C.sub.3 -C.sub.6)-cycloalkyl group, optionally substituted with halogen atoms;R.sub.2 represents one from the following groups: ##STR3## wherein: R.sub.3 represents an F atom, a (C.sub.1 -C.sub.5)-aklyl, an alkyloxy, an alkylthio, an alkylsulfinyl, or an alkylsulfonyl group; andY.sub.1 is either O or CH.sub.2.Type: GrantFiled: October 14, 1992Date of Patent: August 24, 1993Assignee: Presidenza Del Consiglio Dei Ministri-Uffico del Ministro per il coordinamento delle Iniziative per la ricerca Scientifica e TecnologicaInventors: Luigi Capuzzi, Franco Bettarini, Paolo Castoro, Sergio Massimini, Vincenzo Caprioli
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Patent number: 5235068Abstract: Acylaromatic compounds ##STR1## (Q: aromatic compound residue; R: straight, branched or cyclic aliphatic group, aromatic group or araliphatic group) are prepared in high yield by a reaction, in the presence of a boron trifluoride complex catalyst, of an aromatic compound with ##STR2## (X: H, Cl, Br; Y: Cl, Br) or with RCOOH in the presence of (XYCHCO).sub.2 O.Type: GrantFiled: July 21, 1992Date of Patent: August 10, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Michitada Kondo, Yuji Ueda, Seiichi Kai, Takayuki Higashii
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Patent number: 5221765Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.Type: GrantFiled: January 24, 1992Date of Patent: June 22, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5208388Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.Type: GrantFiled: September 20, 1991Date of Patent: May 4, 1993Assignee: Bayer AktiengesellschaftInventors: Karl-Rudolf Gassen, Bernd Baasner
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Patent number: 5206389Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.Type: GrantFiled: June 27, 1991Date of Patent: April 27, 1993Assignee: AtochemInventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
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Patent number: 5196541Abstract: There is described a new process for the preparation of substituted 3-aminoacrylic esters of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and n have the meaning given in the description.The 3-aminoacrylic esters of the formula (I) are obtained by reacting acetic esters of the formula (II)R.sup.1 --(X).sub.n --CH.sub.2 --COOR.sup.Type: GrantFiled: August 2, 1991Date of Patent: March 23, 1993Assignee: Bayer AktiengesellschaftInventors: Herbert Gayer, Alexander Klausener, Peter C. Knuppel, Fritz Maurer
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Patent number: 5185463Abstract: Racemic Feist's acid is treated with (R)-(+)-.alpha.-methylbenzylamine to yield (1R-trans)-3-methylenecyclopropane-1,2-dicarboxylic acid, (R)-.alpha.-methylbenzylamine (1:1) salt. This salt can then be converted to (1R-trans)-3-methylene-1,2-cyclopropanedicarboxylic acid, dimethyl ester which is an intermediate in the preparation of the antiviral agent [1R-(1.alpha.,2.beta., 3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-pur in-6-one. The improved process also enables the recovery of racemic Feist's acid from the resolution.Type: GrantFiled: October 2, 1991Date of Patent: February 9, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: Jollie D. Godfrey, Jr., Richard H. Mueller, Thomas P. Kissick, Janak Singh
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Patent number: 5180741Abstract: Pyrenthrinoid esters with an indenyl nucleus having the following structural formula ##STR1## wherein the substituents are herein defined, have been shown to be useful as pesticides and in pesticidal compositions.Type: GrantFiled: June 11, 1991Date of Patent: January 19, 1993Assignee: Roussel UclafInventors: Didier Babin, Jean-Pierre Demoute, Jean Tessier
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Patent number: 5177109Abstract: Compounds, compositions and methods are described for treating a CNS disorder such as a cognitive disorder, epilepsy, depression, Parkinson's disease, Alzheimer's disease, a neurodegenerative disease or neurotoxic injury. Compound of interest are 2-amino-4,5-methyleneadipic acid compounds and derivatives defined by the formula I: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, ##STR2## with each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein each of X and Y is independently selected from hydroxyl, alkoxy, alkylthio, amino and ##STR3## with each of R.sup.6 and R.sup.7 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein any of R.sup.1 through R.sup.Type: GrantFiled: July 19, 1991Date of Patent: January 5, 1993Assignee: G. D. Searle & Co.Inventors: Roberto Pellicciari, Benedetto Natalini, Maura Marinozzi, Alexis A. Cordi, Joseph B. Monahan, Thomas H. Lanthorn
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Patent number: 5175311Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation.Type: GrantFiled: March 29, 1990Date of Patent: December 29, 1992Assignee: Research Corporation Technologies, Inc.Inventor: Michael F. Doyle
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Patent number: 5164526Abstract: Compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represent hydrogen, alkyl, alkenyl, cycloalkyl, aryl or aralkyl are produced by a new environmentally acceptable process.Type: GrantFiled: October 2, 1990Date of Patent: November 17, 1992Assignee: Biochemie Gesellschaft m.b.H.Inventor: Ingolf Macher
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Patent number: 5159111Abstract: Novel intermediates for fungicides, comprising fluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl,X represents hydrogen, chlorine or bromine andR.sup.1 represents hydroxyl, alkoxy, alkyl or halogen.Type: GrantFiled: September 13, 1991Date of Patent: October 27, 1992Assignee: Bayer AktiengesellschaftInventors: Karl-Rudolf Gassen, Bernd Baasner
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Patent number: 5157146Abstract: A process is provided for preparing isoprenoid cyclopropane 1,1-dicarboxylates which are useful in preparing squalene synthetase inhibitors which inhibit cholesterol biosynthesis, and also useful in preparing pyrethrin insecticides.Type: GrantFiled: October 24, 1991Date of Patent: October 20, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Scott A. Biller, Cornelia Forster
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Patent number: 5149869Abstract: A process for the production or R,S-2,2-dimethylcyclopropanecarboxylic acid starting from isobutylene oxide and a phosphonoacetic acid trialkyl ester. In this way, first the R,S-2,2-dimethylcyclopropanecarboxylic acid-C.sub.1 -C.sub.4 alkyl ester is formed, which then is hydrolyzed to the corresponding acid. R,S-2,2-Dimethylcyclopropanecarboxylic acid is an important intermediate product for the production of S-(+)-2,2-dimethylcyclopropanecarboxamide.Type: GrantFiled: December 6, 1991Date of Patent: September 22, 1992Assignee: Lonza Ltd.Inventors: Thomas Meul, Ulrich Kampfen
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Patent number: 5147645Abstract: Benzyl esters of the formula I ##STR1## where R.sup.1 is methyl, ethyl, halogen, methoxy or ethoxy, R.sup.2 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, C.sub.1 -C.sub.5 -alkyl-substituted cycloalkyl, C.sub.1 -C.sub.5 -substituted cycloalkenyl, C.sub.1 -C.sub.5 -alkyl-substituted bicycloalkyl or C.sub.1 -C.sub.5 -alkyl-substituted bicycloalkenyl, R.sup.3 is hydrogen, cyano, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkyl, A is the carboxylate radical of an acid component typical for pyrethroids and X is hydrogen or halogen, with the proviso that R.sup.2 is not CH.sub.2 --CH.dbd.CH--B when B is hydrogen, alkyl or alkenyl and at the same time R.sup.1 is methyl or halogen, and furthermore with the proviso that R.sup.2 is not methyl when R.sup.1 is methyl, their manufacture, their use for combating pests, and precursors for manufacturing the benzyl esters.Type: GrantFiled: October 1, 1990Date of Patent: September 15, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Wolf, Hans Theobald, Winfried Zombik, Norbert Goetz, Jochen Wild, Albrecht Harreus, Peter Hofmeister, Christoph Kuenast, Jacobus J. DeKramer
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Patent number: RE34652Abstract: Novel fluorinated, acrylamide monomers are prepared from 2-alkenyl azlactones reacted with fluorinated alcohols. The novel monomers have the formula ##STR1## wherein R.sup.1 and R.sup.6 are independently hydrogen or methyl;R.sup.2 and R.sup.3 independently can be an alkyl, cycloalkyl, or aryl group, or R.sup.2 and R.sup.3 taken together with the carbon to which they are joined can form a carbocyclic ring containing 4 to 12 ring atoms;R.sup.4 and R.sup.5 are independently hydrogen or lower alkyl;a is 0 or 1;b is 1 or 2;X is a single bond, CH.sub.2, CH.sub.2 OCH.sub.2, and CH.sub.2 CH.sub.2 OCH.sub.2 ; andR.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group when b is 1 and perfluorinated alkylene when b is 2.Novel polymers and copolymers can be prepared from the monomers of the invention.Type: GrantFiled: June 3, 1992Date of Patent: June 28, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen, Howell K. Smith, II